1-acetyl-6-oxo-8a-methyl-3,4,6,7,8,8a-hexahydronaphthalene



Patented Oct. 14, 1952 l-ACETYL-G- X0-8a-METHYL-3,4,6,7,8,8a-HEXAHYDRONAPHTHALENE Melvin S. Newman and Sambasiva Swaminathan,

Columbus, Ohio, assignors to The University Research Foundation,

Ohio State Columbus,

Ohio, a corporation of Ohio No Drawing. Application August 21, 1951,Serial No. 242,982

1 Claim. 1

The invention disclosed in this application relates to new compositionsof matter.

The object of this invention is to produce a new composition of matterconsisting of a lacetyl-6-oxo-8a-methyl-3,4,6,7,8,8a.hexahydronaphthalene.

This new compound is useful as an intermediate for the total synthesisof steroids and so far as we know has never heretofore been conceived orsynthesized. As a starting point for this compound we can use8a-methyl-l,2,3,4,6,7,- 8,8a-octahydro-l-ethynyl 1 hydroxy 6 0x0-naphthalene. This starting compound is disclosed and the process makingit is disclosed in application for U. S. Patent Serial No. 218,410. Inorder to produce the new composition of matter we react the abovedescribed startin material with formic acid by dissolving it in formicacid. The starting compound has a formula as follows:

OH H Cl) O OH:

It will be noted that not only are the ethynyl and hydroxyl radicals (i.s. OH 02011) converted into the acetyl radical but also the 1 and 2carbons become unsaturated through the introduction of a double bondbetween them.

2 Following is an example of the process we have used to produce ournovel composition of matter.

EXAMPLE O OH: H C

1 -acetyl-6-0xo-8u-methyl-3,4,6,7,8,8a-hexa;hy-

dronaphthalene IX ethanol; yield, 350 mg.; M. P. 143145.

After a similar recrystallization, the product melted at 145.5-147, andwas analyzed.

Analysis:

Calcd. for Cl3Hl602I C, 76.4; H, 7.9 Found: C, 76.1, 76.3; H, 7.6, 7.7

thalene.

MELVIN S. NEWMAN. SAMBASIVA SWAMINATHAN.

REFERENCES CITED The following references are of record in the file ofthis patent:

Friedman et al., Chemistry and Industry, Sept. 15, 1951, pp. 777-8.

